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8 Amazing Ways to Wear Shirtdress with High Boots

By Kaia Saunders / September 7, 2016
Woman in denim shirtdress with flannel-shirt

There is a reason guys like it when their women wear their shirts while in the house. Most guys will say it is because it is revealing yet it gives room for imagination which makes it super sexy.

A shirt dress is a casual shirt though its design is extended to create a dress. The variety of shirt dress in the market is one you cannot get enough of from variation in lengths, hemlines, and lengths of the sleeves can make you fit in a red carpet event to a casual office wear.

Although, we can wear the same outfit but one be mistaken to be going to a red carpet event is how you combine and blend your outfit and accessories. In this article, we will focus on how to combine properly shirt dress and high boots.

How to combine shirtdress with long boots

The shirtdress design and fabric may be great but it is the shoes that set the tone for the outfit. Since more shirtdresses are not accessorized you can try to wear it with a cinched at the waist with a belt. I usually prefer thin belts in case you have to wear one. You can also leave it unbelted to show the effortless sophistication of the entire look. Just so you know I love it effortless.

The biggest issue then you want to wear your amazing shirtdress with high boots is to choose which boots will make a good combo with it. Shirtdresses are classy yet flirty so no matter what you do; do not take away these qualities from your outfit.

When you decide to wear a long shirtdress then ankle-high boots will be the most appropriate. However, this exception is just for a delicately designed shirtdress that may have a longer slit; then you can wear knee-high boots. I always repeat this time to time and in this article I will echo the same thing till you digest it to avoid being captioned by fashion cops; always let your boots style match your shirtdress style.

I mostly do short shirtdresses so I have a lot we can discuss here. Does your body size matter when you consider wearing short shirtdress? NO! It does matter as long as you blend well your outfit. The length of your hemline will determine how high your boots go. I wore thigh-high boots with a very short shirtdress and it was IT. However, depending on how generous you feel showing off your legs you can try it with ankle-high boots. I will try and look at some pictures on how to blend well your shirtdress and high boots to make heads turn as you walk down the streets. I love attention and any decent outfit that can make me look classy and the same time makes heads turn; am definitely down for it.

You can always incorporate hats and leggings or tights to your outfit to make it more fun yet preserved. However, leggings or tights can only be worn when you are wearing a short shirtdress and ankle-high boots so that you do not appear overdressed.

Sassy and classy looks with shirtdress

There are some days you just want to dress to impress because you going to that event you have been waiting for all year. When you choose to wear shirtdress and high boots you have to know the dos and don’ts. You want to steal the show so you go for a short shirtdress but still do not want to reveal the full package.

1. Ms. Boss Flawless Shirtdress Outfit


Collage of woman in blue shirtdress and leather knee high boots

Ms. Boss short blue shirtdress and leather knee high boots just looks awesome (photo:

The pastel color complements Ms. Boss’s physique. This cute and flirty dress is complemented by the leather jacket and high boots which add a little more show to the outfit. To play around with colors she applies a red lipstick to make the statement.

The black leather boots and jacket are used in this outfit to make a personality statement. With a silver necklace and black top inside you can just fall in love with the outfit combo. Now this is a red carpet outfit, my friends! To maintain a classy look when wearing a mini shirtdress, it is better to wear knee high boots so that you avoid showing to much yet it can tease a little. Since you are wearing a high boot just leave a few inches of “leg peak” between the hemline of the shirtdress and the top of the boots.

2. Here she comes!!!

Woman in striped shirtdress and brown knee-high boots

The sexy model combines striped shirtdress and brown knee-high boots that are just gorgeous (photo:

The boot style and shirtdress style are the same which brings out the outfit perfectly. The clutch bag is used to bring the classy look to the outfit.

3. Shirtdress is flirty!! She portrays the theme

Model in black long shirtdress

Beautiful model rolling with a long shirtdress (photo:

The laced up knee-high boots with the long black shirtdress did it for this flawless looking model. She wears the belt to show a little effort to the outfit.

4. Sazan Hendrix Red Carpet Look

Woman in denim shirtdress

Sazan Hendrix looks phenomenon with denim shirtdress (photo:

The dark blue denim and a golden statement necklace and aria boots just did it for Sazan. She accessorized it with a red band to bring more fun to the look and the golden necklace just portrayed the royalty in the outfit. She wore this outfit during the Reem Acra’s SS15 show.

When you are confident abut your legs do not be shy to show them off when wearing a short shirtdress. Let your outfit speak for you! The combination of a short shirtdress and knee-high boots goes well with people who have a daring taste in fashion.

Casual and Funky Look

This is the time you show your creativity in fashion because you are not restricted on what to wear by your job ethics. You can never go wrong with dark denim on a casual Friday. You do not want to be overdressed but you have to pull your A game even when it is just a pizza time out or drinks with your pals. The shirtdress is usually comfy so you can do all the activities on your fun day out without second guessing your outfit.

The first rule of wearing a shirtdress is to ensure that your shirtdress style matches your boots style. You do not want to look like a clown but if you are daring you can mix prints which will bring out the daring personality in you. For casual days I would prefer minimal accessories because it’s a fun day with friends and you might plan for a pizza date and then an impromptu swimming. Friends are unpredictable when together.

You can still rock a casual and funky look with a shirtdress and high boots even on chillier days. It is important to know how to blend the outfit so that you remain warm yet fun. You do not want to freeze to death trying to impress. Tights or leggings usually go a long way in complementing shirtdress in cold weather. They keep you warm yet do not steal the show from the shirtdress making your outfit rock the way you want it to.

5. Britney Walls Killing the Look

The long high slit shirtdress looks superb on Britney Walls (photo:

The long high slit shirtdress looks superb on Britney Walls (photo:

Britney Walls rocks a long shirtdress with black knee-high boots to compliment the long slit on the shirtdress.

6. Cold Weather Is No Excuse to Store Your Shirtdress

Asian girl in jungle green shirtdress

She knows how to compliment her personality with jungle green shirtdress (photo:

The jungle green shirtdress and combat boots and sheer tights made her look flawless. The maroon belt is used as an accessory to break any fashion boredom.

During cold weather you can wear sheer tights or prints depending on the boots and shirtdress style. Try out neutral colors I case you fear that the tights may kill your look.

7. Crop Top and Shirtdress Combo

A very stylish look: black shoes in a matching black and white outfit (photo:

A very stylish look: black shoes in a matching black and white outfit (photo:

She tries something out of the ordinary and nails it. The crop top worn on top of the shirtdress and knee-high boots brings out the street vibe in the outfit. This is both warm and classy.

Shirtdress usually has a street-chic vibe in it and customizing your own ways to bring out the street-chic vibe in it differently is what will make your outfit noticed. You can try out the new outfit with shirtdress but when you are not sure you can start with neutral colors then add more color to bring out the fun personality in you.

8. Creative? You tell Me…

Woman in denim shirtdress with flannel-shirt

Isn’t she pretty: look how flannel-shirt fits with rocking denim shirtdress (photo:

She brings out the street funk with the combo in her outfit. The hat is a great addition to the outfit with the black leather knee-high boots. The flannel-shirt is used as an accessory to enhance a feminine street vibe.

Testing your fashion limits is a great way of coming up with great outfit combos. Dressing up is one thing but making a fashion statement is a whole new dimension. To me, I think this is a fashion statement because she pulled out an outfit that requires you to be daring.

I can advise you that wearing a shirtdress is soft and comfy but you have to take the look a little bit further than the normal. Let your body speak to you as you dress and though you can get great tips from blogs, Pinterest, or even friends on how to pull out shirtdress outfit but your instincts and motivation are what will make you noticed.